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Leaving your life up to chance would of course be a tremendously silly notion.  However, what I think Schwartz's advice means  is to expect less choices and, when choices are presented to us, for us to try not to become overwhelmed.   On page six, Schwartz writes, as one of his five arguments, "We would be better off if we lowered our expectations about the results of decisions."  Lowering our expectations would, in a way, leave some things (the results/consequences of our deicisions) up to serendipity.  We certainly would have a lot less stress regarding our choices, but depending on serendipity is too close to apathy for my liking.  Yet sometimes opportunities come along in life where your only choice is either to dive in head first (isn't that redundant, because diving is always done head first, or is the saying to jump in head first?) or pass it up. 

I've made a few big decisions in my life where the results of which were left to serendipity.  When I finished third grade, I permanently moved in with my mom, who'd been living with my stepdad for a few months in Elkins Park, Pennsylvania (I grew up in Haddon Township, New Jersey, sometimes known as Westmont).  I never thought about how that move would effect my life, but I can easily say now that it was the best decision for my education and happiness.  Applying to Bryn Mawr was also a decision I thought little of at first (the results of my applying were initially not of much importance to me), but soon before I was accepted it had become my top choice and the best fit for me.  Otherwise, I only would have had the option of two similar colleges.

There are also some choices we make whose results cannot be forseen.  Leaving the "Supa Fun" Haverford dance led me to sit with a girl on the blue bus who is now my closest friend at college.  It was a trivial decision, so I did not think of the possible results.  I think Schwartz has the impression to overthink these trivial things.  I do not because I would rather not be bombarded with the vastly frightening array of outcomes some choices yield.  Perhaps an understanding of what is trivial would allow us to leave more things up to serendipity.

ps. You have no idea how hard it is for me to avoid making some sort of pun/horrible joke in my subject line.  In case you didn't have a [typical] childhood, it was a Monopoly pun.